16(R/S)-hydroxycleroda-3,13(14)-dien-16,15-olide - Compound Card

16(R/S)-hydroxycleroda-3,13(14)-dien-16,15-olide

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16(R/S)-hydroxycleroda-3,13(14)-dien-16,15-olide

Structure
Zoomed Structure
  • Family: Plantae - Annonaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpene
Canonical Smiles O=C1OC(C(=C1)CC[C@@]1(C)[C@H](C)CC[C@@]2(C1CCC=C2C)C)O
InChI InChI=1S/C20H30O3/c1-13-6-5-7-16-19(13,3)10-8-14(2)20(16,4)11-9-15-12-17(21)23-18(15)22/h6,12,14,16,18,22H,5,7-11H2,1-4H3/t14-,16?,18?,19+,20+/m1/s1
InChIKey LVSCWEDTMWAASP-DSTASKPNSA-N
Formula C20H30O3
HBA 3
HBD 1
MW 318.46
Rotatable Bonds 3
TPSA 46.53
LogP 4.37
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 318.22
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Polyalthia longifolia Annonaceae Plantae 235806

Showing of synonyms

  • Edmond M.P, Mostafa N.M, et al. (2021). Two clerodane diterpenes isolated from Polyalthia longifolia leaves: comparative structural features, antihistaminic and anti-Helicobacter pylori activities. Nat Prod Res, 2021, 35(23), 5282-5286.. [View] [PubMed]
Pubchem: 102234438

No compound-protein relationship available.

Structure

SMILES: C1OC(=O)C=C1CCC(CCC2)C(C23)CCC=C3

Level: 1

Mol. Weight: 318.46 g/mol

Structure

SMILES: C1=CCCC(C12)CCCC2

Level: 0

Mol. Weight: 318.46 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 318.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.74
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.73
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.94

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.15
Plasma Protein Binding
60.64
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.85
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.88
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.48
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.15
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-0.47
Rat (Acute)
2.13
Rat (Chronic Oral)
1.61
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
373.8
Hydration Free Energy
-4.32
Log(D) at pH=7.4
3.46
Log(P)
4.06
Log S
-5.12
Log(Vapor Pressure)
-6.1
Melting Point
139.61
pKa Acid
8.69
pKa Basic
6.52
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8464
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8044
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7753
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7691
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7529
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7416
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7407
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7381
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7161
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7149
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7144
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7111
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7039
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7016

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